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APPENDIX                                      261

1 The remaining- hydroxyls can always be replaced by chlorine
by the action of I'd... The chlorhyclrins may also be obtained
by the action of MOCl on the olcfines. It is a general property
of these compounds to form the oxide when heated with caustic
alkalis. Ethylenc chlorhydrin gives cthylene oxide in this way,

CUXl.CIL/lII + NaOII = GIL,. GIL, + NaCl + ILO.


Compounds like cthylene oxide and epichlorhydrin may be
regarded as inner ethers,

/GIL,                       /CH,

o<|  -               o/    3

XCH2                      \CH3

TCthylene oxide.                     Dimethyl ether.

These oxide:; are easily decomposed. With water, ethylene oxide
forms glycol ; with hydrochloric acid, the chlorhydrin ; with hydro-
cyanic acid, the cyanhydrin. PZpichlorhydrin behaves similarly.

Succillic Acid.  Tartaric acid, like malic acid, is converted
into succinic acid on reduction with HI, and the relationship of
these three acids is thereby established. The constitution of
succinic acid itself has been determined by its synthesis from
ethyienc (Maxwell Simpson). Ethylene unites with bromine,
forming ethyienc bromide, which yields ethylene cyanide with
potassium cyanide. The latter is then bydrolysecl.
CM,          ClUir          CII,CN          CHo.COOH
CH,   "^   CIU5r    "^    CIIgCN    "^    CII2.COOH
it is an interesting fact, not yet fully explained, that the
alkyl succinic acids give anhydrides more readily than succinic
acid, and the greater the number of alkyl groups, the more
readily is the anhydride produced. Thus the anhydride of
tetramethyl succinic acid is so stable that it is not decomposed
by water.
The symmetrical dialkyl succinic acids exist in two forms,
each yielding a separate anhydride. From their similarity to